# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_General _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- CIF.cif' _audit_creation_date 2012-03-19 _audit_creation_method 'by CrystalStructure 4.0' #============================================================================== _publ_section_references ; Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. SHELX97 Carruthers, J.R., Rollett,J.S., Betteridge, P.W., Kinna, D., Pearce, L., Larsen, A., and Gabe, E.(1999) CRYSTALS Issue 11, Chemical Crystallography Laboratory, Oxford, UK. Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. ; loop_ _publ_author_name 'Yoshihiro Miyake' 'Yuya Ashida' 'Kazunari Nakajima' 'Yoshiaki Nishibayashi' _publ_contact_author_name 'Yoshiaki Nishibayashi' _publ_contact_author_email ynishiba@sogo.t.u-tokyo.ac.jp #============================================================================== data_C23H21NO _database_code_depnum_ccdc_archive 'CCDC 877717' #TrackingRef '- CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C23 H21 N O' _chemical_formula_moiety 'C23 H21 N O' _chemical_formula_weight 327.43 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,+Y,1/2+Z 3 1/2+X,-Y,+Z 4 -X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 17.419(7) _cell_length_b 10.587(5) _cell_length_c 9.567(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1764.5(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1095 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.44 _cell_measurement_temperature 183 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696.00 _exptl_absorpt_coefficient_mu 0.0747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.235 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 183 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 12689 _diffrn_reflns_av_R_equivalents 0.1223 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2145 _reflns_number_gt 1542 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1192 _refine_ls_wR_factor_ref 0.1060 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2145 _refine_ls_number_parameters 247 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[2.6050\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.807 _refine_diff_density_min -0.715 _refine_ls_extinction_method none loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.47433(17) 0.3539(3) 0.5432(4) 0.0505(13) Uani 1.0 4 d . . . N(1) N 0.2904(2) 0.0091(4) 0.7215(5) 0.0343(13) Uani 1.0 4 d . . . C(1) C 0.3305(3) 0.1010(5) 0.8100(5) 0.0384(17) Uani 1.0 4 d . . . C(2) C 0.3747(3) 0.2034(5) 0.7358(6) 0.0353(17) Uani 1.0 4 d . . . C(3) C 0.3661(3) 0.2258(5) 0.6006(5) 0.0336(17) Uani 1.0 4 d . . . C(4) C 0.4065(3) 0.3261(5) 0.5227(6) 0.0348(17) Uani 1.0 4 d . . . C(5) C 0.4251(4) 0.2755(5) 0.8343(6) 0.055(2) Uani 1.0 4 d . . . C(6) C 0.3317(3) -0.1036(5) 0.6872(6) 0.0332(17) Uani 1.0 4 d . . . C(7) C 0.3628(3) -0.1790(5) 0.7897(5) 0.0371(18) Uani 1.0 4 d . . . C(8) C 0.4048(3) -0.2840(5) 0.7539(6) 0.0419(19) Uani 1.0 4 d . . . C(9) C 0.4122(3) -0.3194(6) 0.6147(7) 0.048(2) Uani 1.0 4 d . . . C(10) C 0.3792(3) -0.2477(5) 0.5118(6) 0.0430(19) Uani 1.0 4 d . . . C(11) C 0.3394(3) -0.1368(5) 0.5477(6) 0.0395(18) Uani 1.0 4 d . . . C(12) C 0.2111(3) 0.0168(5) 0.7000(5) 0.0295(16) Uani 1.0 4 d . . . C(13) C 0.1684(3) -0.0909(5) 0.6690(5) 0.0340(16) Uani 1.0 4 d . . . C(14) C 0.0900(3) -0.0839(6) 0.6504(6) 0.0396(18) Uani 1.0 4 d . . . C(15) C 0.0516(3) 0.0298(6) 0.6622(6) 0.0462(19) Uani 1.0 4 d . . . C(16) C 0.0937(3) 0.1373(6) 0.6904(6) 0.0486(19) Uani 1.0 4 d . . . C(17) C 0.1729(3) 0.1304(5) 0.7080(6) 0.0379(17) Uani 1.0 4 d . . . C(18) C 0.3628(3) 0.3996(5) 0.4159(6) 0.0336(16) Uani 1.0 4 d . . . C(19) C 0.2831(3) 0.4094(5) 0.4205(6) 0.0408(18) Uani 1.0 4 d . . . C(20) C 0.2449(4) 0.4832(5) 0.3247(6) 0.049(2) Uani 1.0 4 d . . . C(21) C 0.2843(3) 0.5463(5) 0.2203(6) 0.0465(19) Uani 1.0 4 d . . . C(22) C 0.3630(3) 0.5346(5) 0.2113(6) 0.0449(19) Uani 1.0 4 d . . . C(23) C 0.4018(3) 0.4647(5) 0.3098(6) 0.0400(18) Uani 1.0 4 d . . . H(1) H 0.3656 0.0528 0.8679 0.0460 Uiso 1.0 4 calc R . . H(2) H 0.2919 0.1403 0.8686 0.0462 Uiso 1.0 4 calc R . . H(3) H 0.3317 0.1750 0.5518 0.0402 Uiso 1.0 4 calc R . . H(4) H 0.4773 0.2685 0.8030 0.0657 Uiso 1.0 4 calc R . . H(5) H 0.4207 0.2410 0.9267 0.0657 Uiso 1.0 4 calc R . . H(6) H 0.4103 0.3628 0.8356 0.0657 Uiso 1.0 4 calc R . . H(7) H 0.3570 -0.1571 0.8832 0.0444 Uiso 1.0 4 calc R . . H(8) H 0.4282 -0.3337 0.8218 0.0502 Uiso 1.0 4 calc R . . H(9) H 0.4395 -0.3915 0.5898 0.0574 Uiso 1.0 4 calc R . . H(10) H 0.3831 -0.2733 0.4191 0.0516 Uiso 1.0 4 calc R . . H(11) H 0.3188 -0.0858 0.4781 0.0474 Uiso 1.0 4 calc R . . H(12) H 0.1929 -0.1688 0.6627 0.0406 Uiso 1.0 4 calc R . . H(13) H 0.0623 -0.1559 0.6265 0.0474 Uiso 1.0 4 calc R . . H(14) H -0.0015 0.0336 0.6539 0.0554 Uiso 1.0 4 calc R . . H(15) H 0.0687 0.2148 0.6946 0.0582 Uiso 1.0 4 calc R . . H(16) H 0.2011 0.2029 0.7277 0.0453 Uiso 1.0 4 calc R . . H(17) H 0.2559 0.3640 0.4874 0.0490 Uiso 1.0 4 calc R . . H(18) H 0.1919 0.4918 0.3308 0.0584 Uiso 1.0 4 calc R . . H(19) H 0.2587 0.5973 0.1565 0.0558 Uiso 1.0 4 calc R . . H(20) H 0.3899 0.5736 0.1393 0.0538 Uiso 1.0 4 calc R . . H(21) H 0.4551 0.4597 0.3057 0.0479 Uiso 1.0 4 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.035(3) 0.053(3) 0.063(3) -0.0030(19) -0.006(2) 0.005(2) N(1) 0.031(3) 0.033(3) 0.039(3) -0.002(3) -0.007(3) -0.005(3) C(1) 0.040(4) 0.039(4) 0.037(4) 0.005(3) -0.001(3) -0.005(3) C(2) 0.025(3) 0.036(4) 0.045(4) -0.000(3) 0.004(3) -0.005(3) C(3) 0.032(3) 0.035(4) 0.033(4) -0.005(3) 0.001(3) -0.008(3) C(4) 0.034(3) 0.032(4) 0.038(4) 0.009(3) 0.010(3) -0.005(3) C(5) 0.051(4) 0.060(5) 0.052(5) -0.009(4) -0.006(4) -0.005(4) C(6) 0.021(3) 0.036(4) 0.043(4) -0.007(3) 0.001(3) -0.002(3) C(7) 0.036(4) 0.045(4) 0.029(4) 0.000(3) -0.002(3) 0.004(3) C(8) 0.033(4) 0.048(5) 0.046(4) -0.000(3) -0.002(3) 0.002(3) C(9) 0.031(4) 0.047(5) 0.066(5) -0.001(3) -0.002(4) -0.006(4) C(10) 0.038(4) 0.055(5) 0.036(4) 0.001(3) 0.003(3) -0.009(4) C(11) 0.039(4) 0.051(4) 0.028(4) -0.003(3) 0.001(3) 0.005(3) C(12) 0.023(3) 0.046(4) 0.019(3) 0.001(3) 0.001(3) 0.001(3) C(13) 0.031(3) 0.041(4) 0.029(3) 0.002(3) -0.001(3) -0.004(3) C(14) 0.029(3) 0.051(4) 0.039(4) -0.011(3) 0.002(3) -0.010(3) C(15) 0.029(3) 0.055(5) 0.055(5) 0.001(3) 0.002(3) -0.009(4) C(16) 0.046(4) 0.049(5) 0.051(4) 0.006(3) 0.002(4) -0.003(4) C(17) 0.032(3) 0.039(4) 0.043(4) -0.004(3) -0.001(3) -0.004(3) C(18) 0.027(3) 0.035(4) 0.040(4) 0.001(3) -0.005(3) -0.004(3) C(19) 0.042(4) 0.043(4) 0.037(4) -0.006(3) 0.002(4) 0.001(3) C(20) 0.035(4) 0.051(5) 0.059(5) -0.002(4) -0.006(4) -0.000(4) C(21) 0.059(4) 0.045(4) 0.035(4) -0.004(3) -0.010(4) 0.008(3) C(22) 0.054(4) 0.045(4) 0.035(4) -0.003(3) 0.003(4) -0.006(3) C(23) 0.040(4) 0.039(4) 0.041(4) 0.007(3) -0.004(4) -0.008(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(4) 1.233(6) yes . . N(1) C(1) 1.467(7) yes . . N(1) C(6) 1.432(7) yes . . N(1) C(12) 1.398(6) yes . . C(1) C(2) 1.507(8) yes . . C(2) C(3) 1.324(8) yes . . C(2) C(5) 1.497(8) yes . . C(3) C(4) 1.477(7) yes . . C(4) C(18) 1.493(8) yes . . C(6) C(7) 1.375(8) yes . . C(6) C(11) 1.386(8) yes . . C(7) C(8) 1.374(8) yes . . C(8) C(9) 1.390(8) yes . . C(9) C(10) 1.370(8) yes . . C(10) C(11) 1.406(8) yes . . C(12) C(13) 1.393(7) yes . . C(12) C(17) 1.377(7) yes . . C(13) C(14) 1.380(7) yes . . C(14) C(15) 1.382(8) yes . . C(15) C(16) 1.381(8) yes . . C(16) C(17) 1.392(7) yes . . C(18) C(19) 1.394(7) yes . . C(18) C(23) 1.403(8) yes . . C(19) C(20) 1.376(8) yes . . C(20) C(21) 1.383(8) yes . . C(21) C(22) 1.378(8) yes . . C(22) C(23) 1.377(8) yes . . C(1) H(1) 0.970 no . . C(1) H(2) 0.970 no . . C(3) H(3) 0.930 no . . C(5) H(4) 0.960 no . . C(5) H(5) 0.960 no . . C(5) H(6) 0.960 no . . C(7) H(7) 0.930 no . . C(8) H(8) 0.930 no . . C(9) H(9) 0.930 no . . C(10) H(10) 0.930 no . . C(11) H(11) 0.930 no . . C(13) H(12) 0.930 no . . C(14) H(13) 0.930 no . . C(15) H(14) 0.930 no . . C(16) H(15) 0.930 no . . C(17) H(16) 0.930 no . . C(19) H(17) 0.930 no . . C(20) H(18) 0.930 no . . C(21) H(19) 0.930 no . . C(22) H(20) 0.930 no . . C(23) H(21) 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(1) N(1) C(6) 116.4(4) yes . . . C(1) N(1) C(12) 121.2(4) yes . . . C(6) N(1) C(12) 120.8(4) yes . . . N(1) C(1) C(2) 116.7(4) yes . . . C(1) C(2) C(3) 122.1(5) yes . . . C(1) C(2) C(5) 111.7(5) yes . . . C(3) C(2) C(5) 126.2(5) yes . . . C(2) C(3) C(4) 124.6(5) yes . . . O(1) C(4) C(3) 123.3(5) yes . . . O(1) C(4) C(18) 118.2(5) yes . . . C(3) C(4) C(18) 118.5(5) yes . . . N(1) C(6) C(7) 121.2(5) yes . . . N(1) C(6) C(11) 118.7(5) yes . . . C(7) C(6) C(11) 120.0(5) yes . . . C(6) C(7) C(8) 120.1(5) yes . . . C(7) C(8) C(9) 120.4(5) yes . . . C(8) C(9) C(10) 120.0(5) yes . . . C(9) C(10) C(11) 119.6(5) yes . . . C(6) C(11) C(10) 119.7(5) yes . . . N(1) C(12) C(13) 120.7(5) yes . . . N(1) C(12) C(17) 121.3(5) yes . . . C(13) C(12) C(17) 118.0(4) yes . . . C(12) C(13) C(14) 120.8(5) yes . . . C(13) C(14) C(15) 121.0(5) yes . . . C(14) C(15) C(16) 118.5(5) yes . . . C(15) C(16) C(17) 120.5(5) yes . . . C(12) C(17) C(16) 121.2(5) yes . . . C(4) C(18) C(19) 121.7(5) yes . . . C(4) C(18) C(23) 120.3(5) yes . . . C(19) C(18) C(23) 118.0(5) yes . . . C(18) C(19) C(20) 120.2(5) yes . . . C(19) C(20) C(21) 121.0(5) yes . . . C(20) C(21) C(22) 119.7(5) yes . . . C(21) C(22) C(23) 119.6(5) yes . . . C(18) C(23) C(22) 121.4(5) yes . . . N(1) C(1) H(1) 106.382 no . . . N(1) C(1) H(2) 106.669 no . . . C(2) C(1) H(1) 109.004 no . . . C(2) C(1) H(2) 108.523 no . . . H(1) C(1) H(2) 109.443 no . . . C(2) C(3) H(3) 117.413 no . . . C(4) C(3) H(3) 118.003 no . . . C(2) C(5) H(4) 108.695 no . . . C(2) C(5) H(5) 109.831 no . . . C(2) C(5) H(6) 109.967 no . . . H(4) C(5) H(5) 109.440 no . . . H(4) C(5) H(6) 109.446 no . . . H(5) C(5) H(6) 109.445 no . . . C(6) C(7) H(7) 119.900 no . . . C(8) C(7) H(7) 119.926 no . . . C(7) C(8) H(8) 121.152 no . . . C(9) C(8) H(8) 118.438 no . . . C(8) C(9) H(9) 120.936 no . . . C(10) C(9) H(9) 119.067 no . . . C(9) C(10) H(10) 119.506 no . . . C(11) C(10) H(10) 120.864 no . . . C(6) C(11) H(11) 120.332 no . . . C(10) C(11) H(11) 120.004 no . . . C(12) C(13) H(12) 119.690 no . . . C(14) C(13) H(12) 119.499 no . . . C(13) C(14) H(13) 120.091 no . . . C(15) C(14) H(13) 118.876 no . . . C(14) C(15) H(14) 120.778 no . . . C(16) C(15) H(14) 120.686 no . . . C(15) C(16) H(15) 119.143 no . . . C(17) C(16) H(15) 120.369 no . . . C(12) C(17) H(16) 118.498 no . . . C(16) C(17) H(16) 120.285 no . . . C(18) C(19) H(17) 119.392 no . . . C(20) C(19) H(17) 120.411 no . . . C(19) C(20) H(18) 119.528 no . . . C(21) C(20) H(18) 119.424 no . . . C(20) C(21) H(19) 121.098 no . . . C(22) C(21) H(19) 119.232 no . . . C(21) C(22) H(20) 120.562 no . . . C(23) C(22) H(20) 119.808 no . . . C(18) C(23) H(21) 119.093 no . . . C(22) C(23) H(21) 119.479 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(1) N(1) C(6) C(7) 54.5(6) no . . . . C(1) N(1) C(6) C(11) -126.2(4) no . . . . C(6) N(1) C(1) C(2) 92.6(5) no . . . . C(1) N(1) C(12) C(13) -153.1(4) no . . . . C(1) N(1) C(12) C(17) 27.3(7) no . . . . C(12) N(1) C(1) C(2) -102.1(5) no . . . . C(6) N(1) C(12) C(13) 11.6(7) no . . . . C(6) N(1) C(12) C(17) -168.0(4) no . . . . C(12) N(1) C(6) C(7) -110.9(5) no . . . . C(12) N(1) C(6) C(11) 68.4(6) no . . . . N(1) C(1) C(2) C(3) 13.0(7) no . . . . N(1) C(1) C(2) C(5) -169.0(4) no . . . . C(1) C(2) C(3) C(4) 178.8(4) no . . . . C(5) C(2) C(3) C(4) 1.1(8) no . . . . C(2) C(3) C(4) O(1) 39.3(8) no . . . . C(2) C(3) C(4) C(18) -139.4(5) no . . . . O(1) C(4) C(18) C(19) -155.8(5) no . . . . O(1) C(4) C(18) C(23) 22.1(7) no . . . . C(3) C(4) C(18) C(19) 22.9(7) no . . . . C(3) C(4) C(18) C(23) -159.2(4) no . . . . N(1) C(6) C(7) C(8) -177.5(4) no . . . . N(1) C(6) C(11) C(10) -179.5(4) no . . . . C(7) C(6) C(11) C(10) -0.2(7) no . . . . C(11) C(6) C(7) C(8) 3.2(7) no . . . . C(6) C(7) C(8) C(9) -4.0(8) no . . . . C(7) C(8) C(9) C(10) 1.6(8) no . . . . C(8) C(9) C(10) C(11) 1.4(8) no . . . . C(9) C(10) C(11) C(6) -2.2(7) no . . . . N(1) C(12) C(13) C(14) 178.8(4) no . . . . N(1) C(12) C(17) C(16) -178.2(4) no . . . . C(13) C(12) C(17) C(16) 2.2(7) no . . . . C(17) C(12) C(13) C(14) -1.6(7) no . . . . C(12) C(13) C(14) C(15) -0.1(7) no . . . . C(13) C(14) C(15) C(16) 1.3(8) no . . . . C(14) C(15) C(16) C(17) -0.7(8) no . . . . C(15) C(16) C(17) C(12) -1.0(8) no . . . . C(4) C(18) C(19) C(20) 176.6(5) no . . . . C(4) C(18) C(23) C(22) -179.0(5) no . . . . C(19) C(18) C(23) C(22) -1.1(8) no . . . . C(23) C(18) C(19) C(20) -1.3(8) no . . . . C(18) C(19) C(20) C(21) 1.7(8) no . . . . C(19) C(20) C(21) C(22) 0.4(8) no . . . . C(20) C(21) C(22) C(23) -2.8(8) no . . . . C(21) C(22) C(23) C(18) 3.1(8) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) C(2) 2.991(6) no . . O(1) C(5) 3.030(7) no . . O(1) C(19) 3.581(6) no . . O(1) C(23) 2.821(7) no . . N(1) C(3) 2.888(7) no . . C(1) C(7) 3.023(8) no . . C(1) C(11) 3.558(8) no . . C(1) C(17) 2.930(7) no . . C(2) C(6) 3.368(8) no . . C(2) C(12) 3.484(7) no . . C(3) C(19) 2.973(7) no . . C(4) C(5) 3.046(8) no . . C(6) C(9) 2.769(8) no . . C(6) C(13) 2.852(7) no . . C(7) C(10) 2.771(8) no . . C(7) C(12) 3.466(7) no . . C(8) C(11) 2.760(8) no . . C(11) C(12) 3.124(7) no . . C(11) C(13) 3.232(7) no . . C(12) C(15) 2.805(7) no . . C(13) C(16) 2.752(8) no . . C(14) C(17) 2.746(8) no . . C(18) C(21) 2.790(8) no . . C(19) C(22) 2.775(8) no . . C(20) C(23) 2.744(8) no . . O(1) C(8) 3.556(7) no . 4_654 O(1) C(22) 3.466(7) no . 4_665 C(8) O(1) 3.556(7) no . 4_655 C(16) C(18) 3.597(8) no . 2_555 C(17) C(18) 3.531(8) no . 2_555 C(18) C(16) 3.597(8) no . 2_554 C(18) C(17) 3.531(8) no . 2_554 C(19) C(21) 3.422(8) no . 2_555 C(21) C(19) 3.422(8) no . 2_554 C(22) O(1) 3.466(7) no . 4_664 O(1) H(3) 3.1248 no . . O(1) H(4) 2.6453 no . . O(1) H(6) 3.0135 no . . O(1) H(21) 2.5556 no . . N(1) H(3) 2.4983 no . . N(1) H(7) 2.6150 no . . N(1) H(11) 2.5840 no . . N(1) H(12) 2.5975 no . . N(1) H(16) 2.5744 no . . C(1) H(3) 2.5921 no . . C(1) H(4) 3.1121 no . . C(1) H(5) 2.4311 no . . C(1) H(6) 3.1100 no . . C(1) H(7) 2.8581 no . . C(1) H(16) 2.6205 no . . C(2) H(16) 3.0243 no . . C(2) H(17) 3.5805 no . . C(3) H(1) 3.1454 no . . C(3) H(2) 3.0109 no . . C(3) H(4) 2.7766 no . . C(3) H(5) 3.2662 no . . C(3) H(6) 2.7847 no . . C(3) H(11) 3.5963 no . . C(3) H(16) 3.1295 no . . C(3) H(17) 2.6456 no . . C(4) H(4) 3.0136 no . . C(4) H(6) 3.0195 no . . C(4) H(17) 2.6763 no . . C(4) H(21) 2.6508 no . . C(5) H(1) 2.5946 no . . C(5) H(2) 2.7458 no . . C(5) H(3) 3.3290 no . . C(6) H(1) 2.4660 no . . C(6) H(2) 3.1875 no . . C(6) H(3) 3.2219 no . . C(6) H(8) 3.2279 no . . C(6) H(10) 3.2571 no . . C(6) H(12) 2.5257 no . . C(7) H(1) 2.5665 no . . C(7) H(9) 3.2410 no . . C(7) H(11) 3.2323 no . . C(7) H(12) 3.2012 no . . C(8) H(10) 3.2278 no . . C(9) H(7) 3.2372 no . . C(9) H(11) 3.2365 no . . C(10) H(8) 3.2183 no . . C(11) H(3) 3.3047 no . . C(11) H(7) 3.2313 no . . C(11) H(9) 3.2363 no . . C(11) H(12) 2.7990 no . . C(12) H(1) 3.1580 no . . C(12) H(2) 2.5084 no . . C(12) H(3) 3.0389 no . . C(12) H(7) 3.5942 no . . C(12) H(11) 3.0339 no . . C(12) H(13) 3.2485 no . . C(12) H(15) 3.2480 no . . C(13) H(11) 3.1929 no . . C(13) H(14) 3.2437 no . . C(13) H(16) 3.2112 no . . C(14) H(15) 3.2125 no . . C(15) H(12) 3.2364 no . . C(15) H(16) 3.2448 no . . C(16) H(13) 3.2106 no . . C(17) H(2) 2.5820 no . . C(17) H(3) 3.1794 no . . C(17) H(12) 3.2160 no . . C(17) H(14) 3.2485 no . . C(17) H(17) 3.5581 no . . C(18) H(3) 2.7631 no . . C(18) H(18) 3.2377 no . . C(18) H(20) 3.2589 no . . C(19) H(3) 2.9071 no . . C(19) H(19) 3.2438 no . . C(19) H(21) 3.2357 no . . C(20) H(20) 3.2309 no . . C(21) H(17) 3.2403 no . . C(21) H(21) 3.2183 no . . C(22) H(18) 3.2237 no . . C(23) H(17) 3.2384 no . . C(23) H(19) 3.2165 no . . H(1) H(3) 3.3424 no . . H(1) H(4) 3.0629 no . . H(1) H(5) 2.2811 no . . H(1) H(6) 3.3865 no . . H(1) H(7) 2.2325 no . . H(1) H(16) 3.5409 no . . H(2) H(3) 3.1316 no . . H(2) H(4) 3.5590 no . . H(2) H(5) 2.5456 no . . H(2) H(6) 3.1465 no . . H(2) H(7) 3.3494 no . . H(2) H(16) 2.1813 no . . H(3) H(11) 2.8588 no . . H(3) H(16) 2.8452 no . . H(3) H(17) 2.4756 no . . H(7) H(8) 2.3193 no . . H(7) H(12) 3.5553 no . . H(8) H(9) 2.3112 no . . H(9) H(10) 2.2801 no . . H(10) H(11) 2.3483 no . . H(11) H(12) 2.9494 no . . H(12) H(13) 2.3047 no . . H(13) H(14) 2.3078 no . . H(14) H(15) 2.3091 no . . H(15) H(16) 2.3310 no . . H(16) H(17) 3.0175 no . . H(17) H(18) 2.3057 no . . H(18) H(19) 2.3206 no . . H(19) H(20) 2.3057 no . . H(20) H(21) 2.2971 no . . O(1) H(8) 2.7230 no . 4_654 O(1) H(9) 2.7990 no . 1_565 O(1) H(13) 2.7165 no . 3_555 O(1) H(20) 2.6507 no . 4_665 O(1) H(21) 3.4223 no . 4_665 N(1) H(11) 3.2634 no . 2_555 C(1) H(14) 3.5804 no . 3_555 C(1) H(17) 3.5922 no . 2_555 C(2) H(13) 3.4685 no . 3_555 C(2) H(14) 3.4002 no . 3_555 C(2) H(18) 3.3903 no . 2_555 C(3) H(13) 3.5063 no . 3_555 C(4) H(8) 3.4622 no . 4_654 C(4) H(9) 3.1118 no . 1_565 C(4) H(13) 3.4055 no . 3_555 C(4) H(15) 3.3807 no . 2_554 C(5) H(10) 3.4394 no . 4_655 C(5) H(13) 3.3570 no . 3_555 C(5) H(15) 3.5084 no . 2_555 C(5) H(18) 3.0658 no . 2_555 C(5) H(21) 3.5061 no . 4_665 C(6) H(14) 3.0155 no . 3_555 C(6) H(19) 3.5484 no . 2_545 C(7) H(13) 3.4854 no . 2_555 C(7) H(14) 3.1060 no . 3_555 C(7) H(19) 3.4219 no . 2_545 C(8) H(14) 3.2581 no . 3_555 C(8) H(15) 3.0028 no . 3_555 C(8) H(18) 3.0015 no . 2_545 C(8) H(19) 3.2487 no . 2_545 C(8) H(21) 3.1084 no . 4_655 C(9) H(4) 3.5898 no . 4_654 C(9) H(5) 3.5207 no . 4_654 C(9) H(14) 3.4001 no . 3_555 C(9) H(15) 3.0408 no . 3_555 C(9) H(18) 3.3999 no . 2_545 C(9) H(19) 3.1300 no . 2_545 C(9) H(21) 3.2998 no . 4_655 C(10) H(4) 3.2078 no . 4_654 C(10) H(5) 3.5803 no . 4_654 C(10) H(14) 3.3622 no . 3_555 C(10) H(19) 3.2211 no . 2_545 C(11) H(14) 3.1480 no . 3_555 C(11) H(19) 3.4524 no . 2_545 C(12) H(1) 3.4686 no . 2_554 C(12) H(2) 3.4303 no . 2_554 C(12) H(11) 2.9201 no . 2_555 C(13) H(1) 3.3115 no . 2_554 C(13) H(7) 2.8570 no . 2_554 C(13) H(10) 3.2032 no . 2_555 C(13) H(11) 2.9664 no . 2_555 C(13) H(19) 3.5385 no . 2_545 C(14) H(1) 3.1618 no . 2_554 C(14) H(4) 3.1318 no . 3_455 C(14) H(7) 2.8259 no . 2_554 C(14) H(10) 3.2941 no . 2_555 C(14) H(11) 3.5154 no . 2_555 C(15) H(1) 3.1726 no . 2_554 C(15) H(5) 3.2105 no . 2_554 C(16) H(1) 3.2896 no . 2_554 C(16) H(5) 2.7627 no . 2_554 C(17) H(1) 3.4225 no . 2_554 C(17) H(2) 3.3060 no . 2_554 C(17) H(3) 3.3236 no . 2_555 C(17) H(5) 3.3575 no . 2_554 C(17) H(11) 3.4551 no . 2_555 C(18) H(9) 3.0735 no . 1_565 C(18) H(10) 3.4811 no . 1_565 C(18) H(15) 3.1196 no . 2_554 C(18) H(16) 2.9705 no . 2_554 C(19) H(2) 3.1730 no . 2_554 C(19) H(6) 3.4989 no . 2_554 C(19) H(16) 2.8741 no . 2_554 C(19) H(19) 3.0960 no . 2_555 C(20) H(6) 2.9905 no . 2_554 C(20) H(8) 3.5853 no . 2_564 C(20) H(16) 3.2490 no . 2_554 C(20) H(17) 3.4646 no . 2_554 C(20) H(19) 3.3970 no . 2_555 C(21) H(10) 3.1972 no . 1_565 C(21) H(12) 3.0920 no . 2_564 C(21) H(17) 3.0297 no . 2_554 C(22) H(4) 3.5860 no . 4_664 C(22) H(10) 2.8655 no . 1_565 C(22) H(12) 3.3201 no . 2_564 C(22) H(15) 3.5923 no . 2_554 C(22) H(17) 3.4834 no . 2_554 C(23) H(4) 3.5238 no . 4_664 C(23) H(8) 3.2709 no . 4_654 C(23) H(9) 3.1506 no . 1_565 C(23) H(9) 3.5589 no . 4_654 C(23) H(10) 2.9827 no . 1_565 C(23) H(15) 2.9111 no . 2_554 C(23) H(16) 3.3937 no . 2_554 H(1) C(12) 3.4686 no . 2_555 H(1) C(13) 3.3115 no . 2_555 H(1) C(14) 3.1618 no . 2_555 H(1) C(15) 3.1726 no . 2_555 H(1) C(16) 3.2896 no . 2_555 H(1) C(17) 3.4225 no . 2_555 H(1) H(13) 3.5467 no . 2_555 H(1) H(14) 3.2225 no . 3_555 H(2) C(12) 3.4303 no . 2_555 H(2) C(17) 3.3060 no . 2_555 H(2) C(19) 3.1730 no . 2_555 H(2) H(3) 2.8003 no . 2_555 H(2) H(11) 3.2468 no . 2_555 H(2) H(16) 3.5005 no . 2_555 H(2) H(17) 2.7561 no . 2_555 H(3) C(17) 3.3236 no . 2_554 H(3) H(2) 2.8003 no . 2_554 H(3) H(16) 3.1668 no . 2_554 H(4) C(9) 3.5898 no . 4_655 H(4) C(10) 3.2078 no . 4_655 H(4) C(14) 3.1318 no . 3_555 H(4) C(22) 3.5860 no . 4_665 H(4) C(23) 3.5238 no . 4_665 H(4) H(9) 3.3645 no . 4_655 H(4) H(10) 2.6749 no . 4_655 H(4) H(13) 2.5434 no . 3_555 H(4) H(14) 3.5216 no . 3_555 H(4) H(20) 3.2555 no . 4_665 H(4) H(21) 3.1093 no . 4_665 H(5) C(9) 3.5207 no . 4_655 H(5) C(10) 3.5803 no . 4_655 H(5) C(15) 3.2105 no . 2_555 H(5) C(16) 2.7627 no . 2_555 H(5) C(17) 3.3575 no . 2_555 H(5) H(9) 3.3013 no . 4_655 H(5) H(10) 3.4363 no . 4_655 H(5) H(14) 3.3949 no . 2_555 H(5) H(15) 2.5845 no . 2_555 H(5) H(16) 3.5994 no . 2_555 H(5) H(17) 3.3908 no . 2_555 H(5) H(18) 3.4268 no . 2_555 H(6) C(19) 3.4989 no . 2_555 H(6) C(20) 2.9905 no . 2_555 H(6) H(8) 3.2312 no . 1_565 H(6) H(9) 3.5444 no . 1_565 H(6) H(9) 3.5847 no . 4_655 H(6) H(17) 3.2378 no . 2_555 H(6) H(18) 2.2436 no . 2_555 H(6) H(21) 3.0192 no . 4_665 H(7) C(13) 2.8570 no . 2_555 H(7) C(14) 2.8259 no . 2_555 H(7) H(11) 3.2814 no . 2_555 H(7) H(12) 2.8142 no . 2_555 H(7) H(13) 2.7192 no . 2_555 H(7) H(14) 3.5497 no . 3_555 H(8) O(1) 2.7230 no . 4_655 H(8) C(4) 3.4622 no . 4_655 H(8) C(20) 3.5853 no . 2_545 H(8) C(23) 3.2709 no . 4_655 H(8) H(6) 3.2312 no . 1_545 H(8) H(13) 3.4740 no . 2_555 H(8) H(15) 3.0095 no . 3_555 H(8) H(18) 2.7925 no . 2_545 H(8) H(20) 3.2613 no . 1_546 H(8) H(21) 2.4362 no . 4_655 H(9) O(1) 2.7990 no . 1_545 H(9) C(4) 3.1118 no . 1_545 H(9) C(18) 3.0735 no . 1_545 H(9) C(23) 3.1506 no . 1_545 H(9) C(23) 3.5589 no . 4_655 H(9) H(4) 3.3645 no . 4_654 H(9) H(5) 3.3013 no . 4_654 H(9) H(6) 3.5444 no . 1_545 H(9) H(6) 3.5847 no . 4_654 H(9) H(15) 3.0932 no . 3_555 H(9) H(18) 3.4769 no . 2_545 H(9) H(19) 3.5133 no . 2_545 H(9) H(20) 3.5733 no . 4_655 H(9) H(21) 3.1535 no . 1_545 H(9) H(21) 2.8562 no . 4_655 H(10) C(5) 3.4394 no . 4_654 H(10) C(13) 3.2032 no . 2_554 H(10) C(14) 3.2941 no . 2_554 H(10) C(18) 3.4811 no . 1_545 H(10) C(21) 3.1972 no . 1_545 H(10) C(22) 2.8655 no . 1_545 H(10) C(23) 2.9827 no . 1_545 H(10) H(4) 2.6749 no . 4_654 H(10) H(5) 3.4363 no . 4_654 H(10) H(12) 2.9987 no . 2_554 H(10) H(13) 3.2075 no . 2_554 H(10) H(19) 3.5894 no . 1_545 H(10) H(20) 3.1314 no . 1_545 H(10) H(21) 3.2776 no . 1_545 H(11) N(1) 3.2634 no . 2_554 H(11) C(12) 2.9201 no . 2_554 H(11) C(13) 2.9664 no . 2_554 H(11) C(14) 3.5154 no . 2_554 H(11) C(17) 3.4551 no . 2_554 H(11) H(2) 3.2468 no . 2_554 H(11) H(7) 3.2814 no . 2_554 H(11) H(12) 3.1496 no . 2_554 H(11) H(14) 3.5966 no . 3_555 H(12) C(21) 3.0920 no . 2_545 H(12) C(22) 3.3201 no . 2_545 H(12) H(7) 2.8142 no . 2_554 H(12) H(10) 2.9987 no . 2_555 H(12) H(11) 3.1496 no . 2_555 H(12) H(19) 2.6166 no . 2_545 H(12) H(20) 3.0934 no . 2_545 H(13) O(1) 2.7165 no . 3_455 H(13) C(2) 3.4685 no . 3_455 H(13) C(3) 3.5063 no . 3_455 H(13) C(4) 3.4055 no . 3_455 H(13) C(5) 3.3570 no . 3_455 H(13) C(7) 3.4854 no . 2_554 H(13) H(1) 3.5467 no . 2_554 H(13) H(4) 2.5434 no . 3_455 H(13) H(7) 2.7192 no . 2_554 H(13) H(8) 3.4740 no . 2_554 H(13) H(10) 3.2075 no . 2_555 H(13) H(20) 2.9852 no . 2_545 H(14) C(1) 3.5804 no . 3_455 H(14) C(2) 3.4002 no . 3_455 H(14) C(6) 3.0155 no . 3_455 H(14) C(7) 3.1060 no . 3_455 H(14) C(8) 3.2581 no . 3_455 H(14) C(9) 3.4001 no . 3_455 H(14) C(10) 3.3622 no . 3_455 H(14) C(11) 3.1480 no . 3_455 H(14) H(1) 3.2225 no . 3_455 H(14) H(4) 3.5216 no . 3_455 H(14) H(5) 3.3949 no . 2_554 H(14) H(7) 3.5497 no . 3_455 H(14) H(11) 3.5966 no . 3_455 H(15) C(4) 3.3807 no . 2_555 H(15) C(5) 3.5084 no . 2_554 H(15) C(8) 3.0028 no . 3_455 H(15) C(9) 3.0408 no . 3_455 H(15) C(18) 3.1196 no . 2_555 H(15) C(22) 3.5923 no . 2_555 H(15) C(23) 2.9111 no . 2_555 H(15) H(5) 2.5845 no . 2_554 H(15) H(8) 3.0095 no . 3_455 H(15) H(9) 3.0932 no . 3_455 H(15) H(21) 2.8326 no . 2_555 H(16) C(18) 2.9705 no . 2_555 H(16) C(19) 2.8741 no . 2_555 H(16) C(20) 3.2490 no . 2_555 H(16) C(23) 3.3937 no . 2_555 H(16) H(2) 3.5005 no . 2_554 H(16) H(3) 3.1668 no . 2_555 H(16) H(5) 3.5994 no . 2_554 H(16) H(17) 3.1064 no . 2_555 H(17) C(1) 3.5922 no . 2_554 H(17) C(20) 3.4646 no . 2_555 H(17) C(21) 3.0297 no . 2_555 H(17) C(22) 3.4834 no . 2_555 H(17) H(2) 2.7561 no . 2_554 H(17) H(5) 3.3908 no . 2_554 H(17) H(6) 3.2378 no . 2_554 H(17) H(16) 3.1064 no . 2_554 H(17) H(19) 2.9632 no . 2_555 H(18) C(2) 3.3903 no . 2_554 H(18) C(5) 3.0658 no . 2_554 H(18) C(8) 3.0015 no . 2_564 H(18) C(9) 3.3999 no . 2_564 H(18) H(5) 3.4268 no . 2_554 H(18) H(6) 2.2436 no . 2_554 H(18) H(8) 2.7925 no . 2_564 H(18) H(9) 3.4769 no . 2_564 H(18) H(19) 3.4196 no . 2_555 H(18) H(20) 3.3900 no . 2_555 H(19) C(6) 3.5484 no . 2_564 H(19) C(7) 3.4219 no . 2_564 H(19) C(8) 3.2487 no . 2_564 H(19) C(9) 3.1300 no . 2_564 H(19) C(10) 3.2211 no . 2_564 H(19) C(11) 3.4524 no . 2_564 H(19) C(13) 3.5385 no . 2_564 H(19) C(19) 3.0960 no . 2_554 H(19) C(20) 3.3970 no . 2_554 H(19) H(9) 3.5133 no . 2_564 H(19) H(10) 3.5894 no . 1_565 H(19) H(12) 2.6166 no . 2_564 H(19) H(17) 2.9632 no . 2_554 H(19) H(18) 3.4196 no . 2_554 H(20) O(1) 2.6507 no . 4_664 H(20) H(4) 3.2555 no . 4_664 H(20) H(8) 3.2613 no . 1_564 H(20) H(9) 3.5733 no . 4_654 H(20) H(10) 3.1314 no . 1_565 H(20) H(12) 3.0934 no . 2_564 H(20) H(13) 2.9852 no . 2_564 H(20) H(18) 3.3900 no . 2_554 H(21) O(1) 3.4223 no . 4_664 H(21) C(5) 3.5061 no . 4_664 H(21) C(8) 3.1084 no . 4_654 H(21) C(9) 3.2998 no . 4_654 H(21) H(4) 3.1093 no . 4_664 H(21) H(6) 3.0192 no . 4_664 H(21) H(8) 2.4362 no . 4_654 H(21) H(9) 3.1535 no . 1_565 H(21) H(9) 2.8562 no . 4_654 H(21) H(10) 3.2776 no . 1_565 H(21) H(15) 2.8326 no . 2_554 #============================================================================== # End of CIF #==============================================================================